New Cyclotrimerization of Aldehydes to Cyclopentenone or Tetrahydrofuran Induced by Dibromotriphenylphosphorane

Marie-Pierre Heck , Christophe Matt , Alain Wagner (1) , Loic Toupet (2) , Charles Mioskowski (3)

1 Institut Gilbert-Laustriat : Biomolécules, Biotechnologie, Innovation Thérapeutique
2 IPR - Institut de Physique de Rennes
3 CAMB - Conception et application de molécules bioactives

alpha-Mono- or alpha-dialkylated aldehydes undergo cyclotrimerization in the presence of dibromotriphenylphosphorane (PPh(3)Br(2)) to afford cyclopentenones or tetrasubstituted tetrahydrofurans in good yields. These transformations proceed by a tandem aldol dimerization/Nazarov reaction or a tandem aldol dimerization/Prins cyclization.

Domaines: Physique Générale [physics.gen-ph]

Marie-Pierre Heck, Christophe Matt, Alain Wagner, Loic Toupet, Charles Mioskowski. New Cyclotrimerization of Aldehydes to Cyclopentenone or Tetrahydrofuran Induced by Dibromotriphenylphosphorane. European Journal of Organic Chemistry, 2010, 2010 (5), pp.966--971. ⟨10.1002/ejoc.200901105⟩. ⟨hal-01073299⟩